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Record Information
Version	2.0
Creation Date	2012-05-31 13:51:35 -0600
Update Date	2015-09-17 15:41:11 -0600
Secondary Accession Numbers	ECMDB01396
Identification
Name:	5-Methyltetrahydrofolic acid
Description	5 methyltetrahydrofolic acid (5-MTHF) is the most biologically active form of the B-vitamin folic acid, also known generically as folate. It is a methylated derivate of tetrahydrofolate (THF, H4F). It is generated by methylenetetrahydrofolate reductase (MTHFR) from 5,10-methylenetetrahydrofolate (5,10-CH2-THF, MTHF) and used to recycle homocysteine back to methionine by 5-methyltetrahydrofolate-homocysteine methyltransferase (MTR) or methionine synthase (MS). 5-MTHF functions, in concert with vitamin B12, as a methyl-group donor involved in the conversion of the amino acid homocysteine to methionine. Methyl (CH3) group donation is vital to many cellular processes.
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xa1575624> Close
Synonyms:	5-Methyl tetrahydrofolate 5-Methyl tetrahydrofolic acid 5-Methyl-5,6,7,8-tetrahydrofolate 5-Methyl-5,6,7,8-tetrahydrofolic acid 5-Methyl-5,6,7,8-tetrahydropteroyl-L-glutamate 5-Methyl-5,6,7,8-tetrahydropteroyl-L-glutamic acid 5-Methyl-tetrahydrofolate 5-Methyl-tetrahydrofolic acid 5-Methyl-THF 5-Methyltetrahydrofolate 5-Methyltetrahydropteroylglutamate 5-Methyltetrahydropteroylglutamic acid Me-THF Methyl folate Methyl folic acid Methyl-H4F Methyl-tetrahydrofolate Methyl-tetrahydrofolic acid Methyl-THF N( 5)-Methyltetrahydrofolate N( 5)-Methyltetrahydrofolic acid N-(4-(((2-Amino-1,4,5,6,7,8-hexahydro-5-methyl-4-oxo-6-pteridinyl)methyl)amino)benzoyl)-L-Glutamate N-(4-(((2-Amino-1,4,5,6,7,8-hexahydro-5-methyl-4-oxo-6-pteridinyl)methyl)amino)benzoyl)-L-Glutamic acid N-(5-Methyl-5,6,7,8-tetrahydropteroyl)-L-glutamate N-(5-Methyl-5,6,7,8-tetrahydropteroyl)-L-glutamic acid N5-Methyl-tetrahydrofolate N5-Methyl-tetrahydrofolic acid N5-methyl-THF N5-methyltetrahydrofolate N5-methyltetrahydrofolic acid N5-methyltetrahydropteroyl mono-L-glutamate N5-methyltetrahydropteroyl mono-L-glutamic acid [(6S)-5-methyl-5,6,7,8-tetrahydropteroyl]glutamate [(6S)-5-methyl-5,6,7,8-tetrahydropteroyl]glutamic acid
Chemical Formula:	C20H25N7O6
Weight:	Average: 459.4558 Monoisotopic: 459.186631567
InChI Key:	ZNOVTXRBGFNYRX-ZGTCLIOFSA-N
InChI:	InChI=1S/C20H25N7O6/c1-27-12(9-23-16-15(27)18(31)26-20(21)25-16)8-22-11-4-2-10(3-5-11)17(30)24-13(19(32)33)6-7-14(28)29/h2-5,12-13,22H,6-9H2,1H3,(H,24,30)(H,28,29)(H,32,33)(H4,21,23,25,26,31)/t12?,13-/m1/s1
CAS number:	134-35-0
IUPAC Name:	(2S)-2-{[4-({[(6S)-2-amino-5-methyl-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)phenyl]formamido}pentanedioic acid
Traditional IUPAC Name:	5-methyltetrahydrofolate
SMILES:	CN1C(CNC2=CC=C(C=C2)C(=O)N[C@H](CCC(O)=O)C(O)=O)CNC2=C1C(=O)NC(N)=N2
Chemical Taxonomy
Description	belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom.
Kingdom	Organic compounds
Super Class	Organic acids and derivatives
Class	Carboxylic acids and derivatives
Sub Class	Amino acids, peptides, and analogues
Direct Parent	N-acyl-L-alpha-amino acids
Alternative Parents	Short-chain hydroxy acids and derivatives Beta hydroxy acids and derivatives Fatty acids and conjugates Acetamides Secondary carboxylic acid amides Secondary alcohols Monocarboxylic acids and derivatives Carboxylic acids Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
Substituents	N-acyl-l-alpha-amino acid Beta-hydroxy acid Short-chain hydroxy acid Hydroxy acid Fatty acid Acetamide Carboxamide group Secondary alcohol Secondary carboxylic acid amide Monocarboxylic acid or derivatives Carboxylic acid Organic nitrogen compound Organooxygen compound Organonitrogen compound Organic oxygen compound Alcohol Carbonyl group Organopnictogen compound Organic oxide Hydrocarbon derivative Aliphatic acyclic compound
Molecular Framework	Aliphatic acyclic compounds
External Descriptors	L-threonine derivative (CHEBI:45826 ) N-acetyl-L-amino acid (CHEBI:45826 )
Physical Properties
State:	Solid
Charge:	-2
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 0.33 g/L ALOGPS logP -0.58 ALOGPS logP -3.8 ChemAxon logS -3.1 ALOGPS pKa (Strongest Acidic) 3.5 ChemAxon pKa (Strongest Basic) 3.54 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 12 ChemAxon Hydrogen Donor Count 7 ChemAxon Polar Surface Area 198.48 Ų ChemAxon Rotatable Bond Count 9 ChemAxon Refractivity 126.68 m³·mol⁻¹ ChemAxon Polarizability 46.56 ų ChemAxon Number of Rings 3 ChemAxon Bioavailability 0 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	5-Methyltetrahydrofolic acid + L-Homocysteine <> Hydrogen ion + L-Methionine + Tetrahydrofolic acid 2 Hydrogen ion + 5,10-Methylene-THF + NADH > 5-Methyltetrahydrofolic acid + NAD 5-Methyltetrahydrofolic acid + L-Homocysteine <> Tetrahydrofolic acid + L-Methionine 5-Methyltetrahydrofolic acid + NADP <> 5,10-Methylene-THF + NADPH + Hydrogen ion 5-Methyltetrahydrofolic acid + NAD <> 5,10-Methylene-THF + NADH + Hydrogen ion L-Homocysteine + 5-Methyltetrahydrofolic acid L-Methionine + Tetrahydrofolic acid 5-Methyltetrahydrofolic acid + NAD(P)(+) > 5,10-Methylene-THF + NAD(P)H 5-Methyltetrahydrofolic acid + L-Homocysteine > Tetrahydrofolic acid + L-Methionine 5-Methyltetrahydrofolic acid + NAD + NADP <> 5,10-Methylene-THF + NADH + NADPH + Hydrogen ion 5,10-Methylene-THF + NADPH + Hydrogen ion + 5,10-Methylene-THF + NADPH > 5-Methyltetrahydrofolic acid + NADP + 5-Methyltetrahydrofolic acid 5-Methyltetrahydrofolic acid + Homocysteine + 5-Methyltetrahydrofolic acid + Homocysteine > Tetrahydrofolic acid + L-Methionine + Tetrahydrofolic acid 2 Hydrogen ion + 5 5,10-Methylene-THF + NADH >5 5-Methyltetrahydrofolic acid + NAD 5 5-Methyltetrahydrofolic acid + L-Homocysteine <> Hydrogen ion + L-Methionine + Tetrahydrofolic acid 2 Hydrogen ion + 5 5,10-Methylene-THF + NADH >5 5-Methyltetrahydrofolic acid + NAD 5 5-Methyltetrahydrofolic acid + L-Homocysteine <> Hydrogen ion + L-Methionine + Tetrahydrofolic acid
SMPDB Pathways:	One Carbon Pool by Folate I PW001735 One carbon pool by folate PW000773 S-adenosyl-L-methionine cycle PW002080
KEGG Pathways:	Cysteine and methionine metabolism ec00270 Metabolic pathways eco01100 Methane metabolism ec00680 Microbial metabolism in diverse environments ec01120 One carbon pool by folate ec00670 Reductive carboxylate cycle (CO2 fixation) ec00720 Selenoamino acid metabolism ec00450
EcoCyc Pathways:	formylTHF biosynthesis I 1CMET2-PWY methionine biosynthesis I HOMOSER-METSYN-PWY
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_3_6) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-01ox-0312900000-1e7ffc57c6bfdc0e8fe9 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-01ox-0924300000-c9fa222e5e77153ca411 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0006-1921000000-012fee21d119d325c696 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0a4i-0001900000-dd3b789dceaf2f1cb9a7 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0904-1245900000-aa2092d5d8304fe7f772 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0006-7951200000-24cf3f653b8a2e0b9b29 View in MoNA MS Mass Spectrum (Electron Ionization) Not Available View in JSpectraViewer
References
References:	Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510 Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:	Gennari, Federico. Process for producing 5-methyltetrahydrofolic acid and its salts. U.S. (1992), 6 pp.
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 15641 HMDB ID HMDB01396 Pubchem Compound ID 439234 Kegg ID C00440 ChemSpider ID 388371 Wikipedia 5-Methyltetrahydrofolate BioCyc ID 5-METHYL-THF EcoCyc ID 5-METHYL-THF Ligand Expo THH

Enzymes